Acid wool dyestuffs



Patented June 17, 1941 UNatTE-D, smrss I 1 2345mm l Ash) wool. warms Ernst: Heinrich; Frankfort-on.-the-MainrFechenheim Germany, assignor to General Aniline & Film Corporation, New

ti'onoor Delaware York, N. Y., a corpora- No Drawing. :Application November 13, 1939, Se-

riah No.; 304,171. 1938' 4 Claims.

My present invention relates to valuable acid wool dyestufis more particularly to those of the general formula:

in which formula X1 stands for a member of. the

group consisting of hydrogen, alkyl, phenyl and benzyl, X2 for a member of the group consisting of hydrogen, acetyl and substituted acetyl, which dyestuffs dye the animal fibers. from am acid bath bluish shades of a remarkable fastness to light and' of a good levellingfpower: Thepresent-new dyestuffs are obtainablezby" condensing 1-amino 4-halogenanthraquinone=Zesulfonic: acids; with amino compounds of j the: generai'i formula:

wherein X1 and X2 have the aforesaid signification. r Y

The dyestuffs, which correspond to the aforesaid general formula, X2 standing for hydrogen,

are for instance in a simple manner obtainable v by carrying out theaforesa-id condensation while using amino compounds containingthe' a-ee'tyl group and splitting off-'the acetyl} groupf ron'if the molecule of the eondensation products bya subsequent treatmentwith-saponifyingagents;

Moreover the present dyestuffs are obtainable by using astheone reaction component l -amino- 2.4-dihalogenoanthraquinones and replacing in the molecule of the condensation products the halogen atom standing in the Z-positioriof the anthraquinone nucleus by the sulfonic acid group by means of sulfite.

In order to further illustrate my invention the following examplesare given,. the parts being by weight and all temperatures in degrees centigrade.

- Example 1 To a solution of 40 parts of l-amino--bromanthraquinone-2-sulfonic.acid:inzabout4000iparts of watery-50- pantsrofathe sulfate'of 4i-aminobene zyl-acetamide' colorless leaflets of 214/2159me1ting point), 84 parts of sodium bicarbonate and 4 parts'ofcuprous chloride are added. The mixture is heated for some hours at 90 to 95, then In Germany September 30,

' blue sh the formed dyestuff' is isolated It corresponds to the formula:

" 0. NH: H l

SOaH

0 NHOCH1NRC 0.05113 The reaction product is filtered ;off while hot and washed out with salt water. Advantageously it is transformed. into the sodium salt by salting it out from an aqueous sodium carbonate alkaline solution. The dyestuff is very similar in its properties tok'thatioffi Example '1. It dyes wool" likewise =c1ear reddish blue shades of: a -:v somewhat more greenish tint thanrtherdyestilff otrExa'mple. .f Example 3 To a solution of 40 parts of. L-amino-l-bromanthraquinone-2'-sulfonic acid in about 4000 parts of water, 27 parts, of 3-aminobenz-yl-methyl-acetamide, 40 partsof sodium bicarbonateand l parts of cuprous chloride are added; The miiiture isv heated for some hourst'at :to and the formed dyestuff of. the formula: I

is isolated. It is very similar in its properties with the dyestuffs-of Examples 1 and 2.

Similar dyestuffs are obtained by replacing the 3 aminobenzyl-methylacetamide by 3 amino benzyl-ethylacetamide or the corresponding 2- or 4-amino compounds.

When subjecting the latter dyestuff of the formula:

0 NHOOHPN to the process of Example 2 the formed dyestuif of the formula:

II I

dyes wool likewise valuable reddish blue shades. Similar dyestuffs are obtainedwhile using as one reaction component 2; 3 or 4-aminobenzylmethyl-methoxyacetamide of the formula:

NH; CO-CHzO CH1 Example 4 A mixture of a solution of 40 parts of l-amino- 4-bromanthraquinohe-2-sulfonic acid in about 4000' parts of water, 35 parts of 4-aminobenzyl-' phenylacetamide, 40 parts of sodium bicarbonate and 4 parts of cuprous chlorideis heated for some hours at 90 to 95. The formed dyestufi is isolated. It corresponds to the formula:

O NH:

| O 0 NH CHz-N and dyes wool greenish blue shades of a good fastness to light and of'a good levelling power.

When using as the one reaction component 4- amino-dibenzylacetamide of the formula:

v oo-ona a very similar dyestuff is obtained.

' Example 5 more water soluble dyestuff is formed. Then the phenol is removed by steam distillation and the formed dyestufi which is identical in its tinctorial behaviour with the dyestuii. of Example 1 is isolated.

I claim: 1. Acid wool dyestufis of the general formula:

in which formula X1 stands for a member of the group consisting of hydrogen, alkyl, phenyl and benzyl, X2 for a. member of the group-consisting of hydrogen, acetyl and substituted acetyl free from solubilizing groups, which dyestuffs dye the animal fibers from an acid bath bluish shades of a good fastness to light "and of a good levelling power.

2. The acid wool dyestuff of the formula:

S OaH o NHQOHPNH-CO-CEB which dyestufi is when dry 2, dark blue powder soluble in concentrated sulfuric acid with a bluish green color, turning to'yellowish green after the addition of paraformaldehyde and dyes wool from an acid bath clear reddish blue shades of a good fastness to light and of a good levelling power.

3. The acid wool dyestuif of the formula:

0 NH: ii I SOaH ' whichdyestufi is when dry a dark blue powder soluble inconcentrated sulfuric acid with a bluish green color, turning to yellowish green after the addition of paraformaldehyde and dyes wool from an acid bath clear reddish blue shades of a good fastness to light and of a good levelling power.

4; The acid wool dyestuif of the formula:

a a: r

which dyestufi is when dry'a dark blue powder soluble in concentrated sulfuric acid with a bluish greencolor, turning to yellowish green after the additio'n'of paraformaldehyde and dyes wool from an-acid bath clear .reddishblue shades of agood fastness to lightand of a-good levelling power.

COOH:

I ERNST. H INRICH. 

